Whilst my anatomy of Chicago activism in the present reposes on newsstands, let’s turn our attention today to Chicago activism past. Every month I interview an author or activist onstage at the Seminary Co-op bookstore on the University of Chicago campus. Last month my guest was Don Rose, a legendary political consultant who, as I said when I introduced him, has been fighting for democracy in the Second City for literally sixty years. (Another sixty years, I joked, and maybe democracy in Chicago will finally arrive.) It was a pleasure to bring old Don out of the shadows, for he’s always been a back-room guy—but what back rooms!

He’s also a certified original bohemian. Born in 1930 to Jewish parents (his dad managed a shoe store), Don took up trumpet in sixth grade at the end of the swing era, heard Dizzy Gillespie and Charlie Parker, “and had a musical epiphany.” (At the Seminary Co-op, he told the story of the time Charlie Parker came to the Beehive on 55th Street near his apartment in Hyde Park. He repaired to the men’s room. “Next thing I know I’m taking a joint leak with the man we thought might be God on earth. Max Roach taxes this tremendous drum break, and the first word Bird says to me is: Max! I named my kid Max.”) He found his way to Paris, ran into a “young bug-eyed African-American writer who I knew from his essays, but he had just published Go Tell Him On the Mountain.” “Jimmy” Baldwin took him to meet Richard Wright, who was by then a little bit nuts: “When we take over,” he said, “you guys”—he waved to the white hipsters in the room—“we’ll save you.” He didn’t meet Samuel Beckett. “That was the one that got away.”

When he returned to Chicago the Trumbull Park Homes riots broke out. It was 1953. A light-skinned black woman was renting a home in a “white” housing project, accidentally. Her family was attacked. Months later, Chicago’s liberal housing commissioner Elizabeth Wood tried to move ten more black families in—and bloody-minded neighborhood whites rioted for days on end. A thousand uniformed police in four shifts patrolled around the clock. High-minded Hyde Park white liberals like Don (“foolish us!”) sallied forth, and “handed out beautifully written pamphlets about brotherhood. Little realizing that we were taking our lives in our hands. because if there was anything worse than a ‘Negro,’ it was a”—he pauses, not pronouncing the word—“______ lover.” And, since it was all but official city policy to ban the papers from printing news about racial strife in Chicago, they worked to get word of the riots into the press. They failed.

Don did, however, have the last laugh. The riots had been all but organized by the top aide to the powerful neighborhood alderman, Emil Pacini. Ten years later, Don was among the organizers for the reform alderman, John Buchanan, who defeated him.

By then, Chicago’s civil rights forces were massing, and Don was at the center of it. A new school commissioner had been hired, Benjamin Willis, with the task of keeping Chicago schools segregated. Which, considering that the black schools were massively overcrowded and the white schools underused, proved difficult. Willis, though, arrived at a solution: turning trailers set up in playgrounds and parking lots into classrooms. An activist with Saul Alinsky who later became a famous journalist—Nicholas von Hoffman—came up with the term “Willis Wagons.” A phrase to organize with. And by the 1963–64 school year, Chicago’s umbrella civil rights group the Coordinating Council of Community Organizations came up with the idea of boycotting all the schools with Willis Wagons. It was Don Rose who came up with a better idea: “I said, ‘Hell, why do that? Why not call a city-wide boycott?’” He was always coming up with crazy ideas like that. “And it worked pretty well.” Every black school in Chicago was about 98 percent empty. The idea spread to other cities: Cincinnati, New York, Boston, Philadelphia.

By then Don Rose had already met Dr. Martin Luther King Jr. For the previous summer, the black labor organizer A. Phillip Randolph had come up with an idea. For a march. On Washington. For jobs and freedom. Which the respectable black leaders in Chicago thought was pretty dumb. “The heads of these groups like the Urban League and the NAACP were pretty much in Richard J. Daley’s pocket. And they weren’t really sure that this ‘March on Washington’ was going to work, and there might be violence, and they didn’t want to be associated with it, so they fobbed off the job of chairman”—to Timuel Black, now, like Don, another living legend, but then a decidedly second-tier figure, head of the Chicago branch of the Negro American Labor Council.

Last laugh once more: Tim Black and Don Rose marshaled two “freedom trains,” several airplanes, and a massive, enthusiastic Chicago contingent to the March on Washington. “And of course Dr. King delivered that great speech, and we were all basking in the light of it.”

Two years later, CCCO was still fighting to get rid of Willis, organizing a protest march of seven or eight thousand people from the South Loop to City Hall. In a harbinger of the 1968 Democratic convention, there were mass arrests in front of the Hilton Hotel on Balbo. Don relates what happened next: “Up pops Dick Gregory—who was never much for organizational discipline! He jumps up in front of the cameras and says, ‘We’re going to march every day until Willis is gone!’”

At the Seminary Co-op, the audience burst into laughter. Don continued: “We didn’t want to show disunity in the movement! So we started daily marches!”

Mike Royko wrote about those marches in his Daley biography, Boss. After they paraded in front of the mayor’s house in the Bridgeport neighborhood, little girls started a new jumprope chant, to the tune of the Oscar Meyer jingle: “Oh, I wish I were an Alabama trooper/ That is what I’d really like to be/ For if I was an Alabama trooper/ Then I could kill a nigger legally.” Chicago, circa 1965.

Dr. King, around then, had announced he would open a Northern front in his freedom movement. All and sundry presumed he would choose Harlem—New York, of course, being the center of the universe. But King found Harlem’s civil rights leadership a nest of competing intriguers. Don helped organize a weekend visit for King to Chicago; one thing that impressed him was the smooth functioning of Chicago’s activist community. It was those daily Dick Gregory marches: “The one good thing about this is that we learned a lot about organizing!”

King came to Chicago. Don Rose was his press secretary. I tell the story of what happened next in Nixonland:

Chicago had an open-housing ordinance, passed in 1963—that was what let Mayor Daley say there was no segregation in Chicago. So married black couples began visiting real estate offices in bucolic white neighborhoods asking to be shown a home They would be told there were none available. A similarly situated white couple would make the same request and would be given the red-carpet treatment. On July 8 alone, in the neighborhood of Gage Park, the testers recorded thirty prima facie violations of the law. Chicago’s power structure wasn’t about to do anything about that. Doing something about it would be to torch the entire moral economy of the city as Mayor Daley and his core constituency understood it.

One day King’s activist army held a vigil at one of the real estate offices upholding segregation—and were set upon by a mob. What to do next? They decided to march through the neighborhoods where blacks were being refused housing. Take a torch, in other words, to the entire moral economy of the city as Mayor Daley and his core constituency understood it—staging the famous confrontation where Martin Luther King was hit in the head by a rock, responding, “I think the people of Mississippi ought to come to Chicago to learn how to hate.”

That idea to march was Don Rose’s. Though, at this point in the interview, the back-room guy grows bashful. “Someone wrote a book called The Great I. That’s what I feel like now. It’s a shame all these people are dead so they can’t call me a liar!”

Don went on to do more, so much more: a leadership role in planning the protests at the 1968 Democratic convention (he couldn’t be a Chicago 8 defendant because “I technically did not cross state lines,” he told me), consultant for a dozen or more of Chicago’s most important anti-machine reform election campaigns, manager of Jane Byrne’s reform campaign for mayor in 1979. That last one turned out to be pretty crushing. He had also laid out a careful, day-by-day strategy for when she took office to break the back of the Great Chicago Machine once and for all. Which, promptly upon assuming office, Mayor Byrne turned her back on. (You can read about that amazing story in this classic of Chicago history.)

Which is the sort of thing with which warriors for justice are so, so familiar: the bitter defeats, setbacks, crushing blows—including, in fact, the result of King’s efforts in Chicago in 1966: an ineffectual “summit agreement” with city fathers that accomplished nothing; followed by the failure on Capitol Hill of the 1966 open housing bill. The two steps backward for every one step in advance. That was my final question to Don in other interviews—“a broader, existential question,” as I put it:

You and your comrades keep on sort of pushing the next frontier of justice and getting it pushed back—taking another bite of the apple and getting your ass kicked; getting rocks thrown at you; having a summit that isn’t really a summit; getting tear-gassed; getting people elected and then seeing them thrown out; again and again and again, one step forward, and one step back, and here we are in Chicago and they’re hording $500 million in TIF money and giving it to rich developers and throwing kids out of their schools—how do you keep going? How do you conceptualize the grand sweep of what you’re trying to do? And how do you cope psychologically with all this frustration, and how do those of us who are fighting for social change make sense of the bitterness we feel in the face of so much wickedness?”

It was a question the premise of which Don adamantly refused. You have to see, he said, how it all added up.

“We had little victories.” He reeled them off, remembering each indelibly: the time, in 1969, when they elected a slate of progressives to a convention to rewrite the Illinois state Constitution; the election of the first reform alderman on the North Side, Dick Simpson, in 1971; the time in 1972 they beat the machine’s states attorney Edward Hanrahan, the man responsible for the raid that murdered Black Panther leader Fred Hampton (with exquisite karmic justice, that’s the only thing history remembers him for); the time they saved the Congressional seat of Ralph Metcalf, the former machine stooge who broke with Mayor Daley over the issue of police brutality (“It’s never too late to go black,” he said), upon which “Daley put up a stooge against him”—and, in 1980, the time “we elected two independent congressmen,” including “a fella named Harold Washington.”

“Very very significant changes took place over this time without you feeling it…. Someone compared it to a Tsunami that might begin as a ripple in the ocean twenty or twenty years ago…. I think, had we had a continual string of losses I might have dropped out, others might have dropped out. But there were enough of these victories over the years that we could see our way clear.”

A word to the wise, from a very wise man: so, frustrated activist, can you. Pile up those little victories. Some day, your tsunami will come. And you may, like Don, see your way clear.